Sodium Carbonate → HCID 44514402, compound

HRID 1931667Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:12].[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([N:26]2[C:30]3=[N:31][CH:32]=[N:33][C:34](Cl)=[C:29]3[CH:28]=[N:27]2)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[C:13]([O:17][C:18]([N:20]1[CH2:21][CH2:22][CH:23]([N:26]2[C:30]3=[N:31][CH:32]=[N:33][C:34]([O:12][C:3]4[CH:4]=[CH:5][C:6]([S:8]([CH3:11])(=[O:9])=[O:10])=[CH:7][C:2]=4[F:1])=[C:29]3[CH:28]=[N:27]2)[CH2:24][CH2:25]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 2-fluoro-4-methanesulfonyl-phenol (Intermediate 1; 112 mg, 0.6 mmol), 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (200 mg, 0.6 mmol) and potassium carbonate (180 mg, 1.3 mmol) in DMF (2 mL) was heated in a microwave oven at 160° C. for 10 min. Saturated sodium carbonate solution was added to the reaction mixture to give a precipitate which was filtered off and dissolved in ethyl acetate. The organic solution was dried (sodium sulfate), filtered, evaporated, and purified by flash chromatography, eluting with 20% ethyl acetate/hexanes, to give 4-[4-(2-fluoro-4-methane-sulfonyl-phenoxy)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (140 mg, 47%) as a white solid.

Workup

customto give a precipitate which
filtrationwas filtered off
dissolutiondissolved in ethyl acetate
dry with materialThe organic solution was dried (sodium sulfate)
filtrationfiltered
customevaporated
custompurified by flash chromatography
washeluting with 20% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-0435519c8e634f0b81a7caf5d7a7d6e6
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188098B2

Reaction notes

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